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$765,000
4 Beds ⋅ 2 Baths ⋅ 1013005 MLS
Welcome To 10 Curlin Lane, A Completely Gut-Renovated 4 Bedroom 2 Full Bathroom Colonial Offering The Perfect Blend Of Modern Design, Comfort, And Convenience In The Heart Of St. James. This Stunning Home Has Been Thoughtfully Redesigned From Top To Bottom With Today’s Buyer In Mind. The Brand-New Kitchen Showcases Elegant White Maple Cabinetry With Crown Moulding And Custom Lighting, Sleek Quartz Countertops, A Custom Tile Backsplash, And Stainless Steel Appliances—Creating A Clean, Sophisticated Space Ideal For Both Everyday Living And Entertaining. Throughout The Home, You’ll Find A Seamless Combination Of Large-Format Tile And Rich Hardwood Flooring, Complemented By Recessed LED Lighting That Enhances The Bright, Open Feel. Both Full Bathrooms Have Been Beautifully Customized With Custom Tile And Quartz Finishes, Delivering A Spa-Like Experience. Major Upgrades Provide Peace Of Mind, Including A New Roof, Cedar Shake Vinyl Siding, Windows, 200 Amp Electric Service And Fully Updated Heating And Cooling HVAC Systems. Additional Conveniences Include A Stackable Washer/Dryer And Flexible First-Floor Bedroom With Generous Closet Space—Perfect For Guests, Home Office Use, Or Multi-Generational Living, And A Finished Lower Level For Playroom, Media Room, Or Creative Space. Step Outside Through Sliding Doors Off The Dining Area To A Convenient Patio And Fully Fenced Quarter-Acre Backyard With Shed, Offering Ample Space For Outdoor Gatherings, Recreation, Or Future Enhancements. A Single-Car Garage Completes The Package. Ideally Located Less Than A Mile From The St. James LIRR Station And Just Minutes From Shopping, Top Tier Dining, And All The Amenities Of The Smith Haven Mall, This Home Delivers Both Lifestyle And Location. A True Turnkey Opportunity—Simply Unpack And Enjoy.

10 Curlin Lane, Saint James
$649,000
3 Beds ⋅ 2 Baths ⋅ 1012238 MLS
Welcome to this beautiful, totally renovated expanded Cape offering the perfect blend of style, comfort, and functionality! This move-in-ready home features 4 spacious bedrooms, 2 full bathrooms, and a bright, open layout filled with natural light. The updated interior showcases modern finishes throughout, making it easy to simply drop your bags and move right in. Enjoy a full basement with outside entrance, providing endless possibilities for additional living space, storage, or recreation. Outside, you’ll find a detached 2-car garage, a beautiful, oversized side yard perfect for entertaining, gardening, or relaxing, and plenty of outdoor space to enjoy. A true turnkey home, don’t miss this incredible opportunity! Just unpack and start making memories...

44 Elizabeth Avenue, Smithtown
$999,999
3 Beds ⋅ 3 Baths ⋅ 1010352 MLS
Set on over half an acre at the end of a quiet Saint James cul-de-sac, this 4 bedroom, 2.5 bath, 3,313 square foot newer construction center hall colonial offers space, flexibility, and a layout that works for the way people actually live. Hardwood floors run throughout the home, starting with a traditional first-floor layout that includes a welcoming foyer, large formal living room, formal dining room, and a comfortable family room with a wood burning fireplace. Off the family room, sliders open to a huge three-season (300 sq ft) room, creating an additional space to relax, gather, or enjoy the view of the property. From there, another set of doors leads outside, giving the home an easy connection between indoor living and the backyard. The eat-in kitchen anchors the main level with a large center island, generous prep space, sliders to the backyard, and a small butler’s pantry connecting the kitchen and dining room. A first-floor laundry room, two-car attached garage, and basement access add function and convenience to the main level. Upstairs, the second floor opens to a beautiful view overlooking the formal living room below, where cathedral ceilings add height and character to the home. The spacious primary bedroom features vaulted ceilings, two large closets, and an oversized primary bath, while the additional bedrooms feel bright and comfortable with large windows that bring in great natural light. The current upstairs setup offers 3 bedrooms, but this level was originally designed as a 4-bedroom layout and can easily be converted back with one simple wall. With generous room sizes and a flexible second-floor layout, the space can adapt to different needs while still keeping an open, connected feel throughout the home. Outside, the .58-acre property offers a private backyard setting with an in-ground pool, paver areas for lounging and entertaining, in-ground sprinklers, and landscaped front and rear grounds. There is room to enjoy the yard in different ways, whether you are hosting, relaxing, or just appreciating having extra space around you. With its cul-de-sac location, generous square footage, newer construction, and flexible layout throughout, this Saint James colonial offers the kind of space that can grow and change with you.

11 Annemarie Drive, Saint James
$2,399,000
6 Beds ⋅ 5 Baths ⋅ 1010665 MLS
Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with expansive living spaces filled with natural light of generous proportion and seamless indoor-outdoor flow creating a tranquil retreat just moments from the harbor, beaches, yacht clubs, vineyards and nature preserves. Set on two beautifully landscaped level acres of property designed for both everyday enjoyment and sophisticated entertaining. This private estate seamlessly blends timeless elegance, modern luxury, and resort-style living. A grand two-story foyer introduces the home's sophisticated interiors, where soaring cathedral ceilings, gleaming hardwood floors, abundant natural light, and exquisite architectural details create an atmosphere of warmth and refinement. Thoughtfully updated throughout, every space has been designed with both everyday comfort and effortless entertaining in mind. The recently renovated chef's kitchen serves as the heart of the home, featuring a dramatic Crawford ceiling, custom crown and box moldings, quartzite-topped center island, and a suite of premium appliances including a Sub-Zero refrigerator, Bosch range, double ovens, microwave drawer, and dishwasher. The kitchen flows seamlessly into the impressive great room, highlighted by a floor-to-ceiling stone wood-burning fireplace and walls of windows overlooking the picturesque grounds. Elegant entertaining spaces continue with a gracious formal living room accessed through glass pocket doors, and a spacious dining room perfectly suited for hosting intimate gatherings or larger celebrations. The main level offers five generously proportioned bedrooms and three full bathrooms, including two recently renovated baths appointed with refined finishes. Upstairs, an expansive loft with hardwood floors overlooking the great room provides additional living and entertaining space and leads to the luxurious primary suite. This private retreat features hardwood flooring, custom closets, detailed millwork, and a stunning newly renovated spa-inspired bath complete with a soaking tub, oversized glass-enclosed shower, dual vanity, and exquisite Italian tile. The outdoor setting is nothing short of extraordinary. Professionally landscaped grounds surround a tranquil in-ground pool, complemented by multiple paver patios designed for elegant outdoor entertaining and relaxation. A sprawling Trex deck extends nearly the entire length of the home, creating a seamless connection between indoor and outdoor living. Additional highlights include a fully finished lower level with a full bath, offering exceptional flexibility for recreation, fitness, guest accommodations, or extended living space. Car enthusiasts will appreciate the rare offering of four garage spaces, including two attached and two detached garages. Recent improvements include extensive interior and exterior painting, newer windows, custom closet systems, wood flooring throughout most of the house and numerous thoughtful upgrades throughout. A wonderful opportunity awaits for you to own this property and reap the rewards of resort living in the White Spruce Farm Community within the Village of Head of the Harbor. Taxes Include Village Taxes of $3,199

15 The Chase, Saint James
$699,999
3 Beds ⋅ 2 Baths ⋅ 1006934 MLS
Welcome to 3 Bayberry Drive in the heart of Saint James! This beautifully updated home has been renovated from top to bottom within the last six years and offers the perfect blend of style, comfort, and functionality. The stunning kitchen, renovated in 2022, features quartz countertops, stainless steel appliances, custom tile backsplash, recessed lighting, glass display cabinetry, and thoughtful designer finishes throughout. The main bathroom was also completely updated in 2022. There is a full basement with an outside entrance. For added convenience, washer and dryer hookups are available on both the main level and in the basement. Additional updates include beautifully refinished hardwood floors on the main level (2022), central air conditioning on the main floor, and ductless split units in the basement for year-round comfort. Step outside to enjoy the private backyard retreat featuring a spacious deck leading to a large patio—perfect for entertaining guests, outdoor dining, or simply relaxing after a long day. Nestled in a picturesque, storybook neighborhood, this home offers a prime Saint James location close to everything the community has to offer. With countless updates and amenities throughout, this is truly a home that must be seen to be appreciated. Schedule your private showing today before this exceptional opportunity is gone!

3 Bayberry Drive, Saint James
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 1011636 MLS
Nestled on 2.5 private acres in the picturesque Village of Nissequogue, this beautifully remodeled Colonial offers a rare opportunity to enjoy peaceful country-style living with seasonal water views of the Nissequogue River in one of Long Island’s most sought-after communities. This well-maintained home features numerous updates, including a newer roof, siding, driveway, eat-in kitchen, and hardwood flooring throughout the first floor. The interior was freshly painted in March 2026, creating a bright and welcoming atmosphere. The spacious den is highlighted by a cozy wood-burning fireplace with a stove insert, perfect for relaxing on cooler evenings. Updated bathrooms add modern comfort, while the full basement and attached two-car garage provide ample storage and functionality. Enjoy tranquil outdoor living from the rear patio, where partial river views can be appreciated during the summer months. The backyard is surrounded by mature trees, offering privacy, serenity, and a peaceful natural setting. Ideally located near local beaches, hiking and nature trails, fine dining, shopping, and Stony Brook University and Medical Center. This exceptional property combines scenic beauty, modern updates, and convenient access to area amenities. Smithtown Schools

451 River Road, Nissequogue
$899,000
3 Beds ⋅ 3 Baths ⋅ 1011789 MLS
Fall in Love with this Beautiful, Warm and Charming L Ranch Set on Private Cul de Sac, Spacious Rooms, Hardwood Floors throughout, All Andersens, Stone WoodBurning Fireplace, Custom Moldings and Recessed Lighting, Custom EIK and Built-Ins, Main Level Laundry, Huge Finished Basement, Economical Gas Hot Water Heating (4 Zones, 7 Years), HW Heater- 5 Years, Newer Roofing- One Layer-2 Years; Close to All Conveniences! Property Tax with Basic Star $15,231

7 Carrie Court, Smithtown
$849,000
4 Beds ⋅ 2 Baths ⋅ 1005767 MLS
Expanded Ranch with Open Floor Plan, Huge Family Room with Pellet Fireplace Insert, 4 Bedrooms, 2 baths, Detached Heated 2 Car Garage, Gunite In Ground Salt Water Pool w/ Loop Loc Cover,150 Amp Service with Transfer Switch for Generator, Desirable Gas Heat, Central Air-5 Years Young, In Ground Sprinklers, Wood Floors, Attic Fan, Large Driveway, Smithtown Schools with HS West, New Stove, Granite Counters, Beautifully Landscaped and MORE !

25 Del Place, Hauppauge
$1,185,000
5 Beds ⋅ 3 Baths ⋅ 1010498 MLS
Welcome to your private retreat, where comfort, space, and timeless charm come together! Set on a beautifully landscaped .71 acre property, this spacious 5 bedroom, 2.5 bath home in the heart of Smithtown, nestled in the beautiful Forestwood section, offers the perfect blend of elegance, functionality, and outdoor living. Featuring gleaming hardwood floors throughout and a thoughtfully designed layout ideal for both everyday living and entertaining. The heart of the home is the beautiful eat-in-kitchen, featuring granite countertops, tons of cabinetry, and plenty of room for casual meals and conversation. For larger gatherings, the formal dining room provides a warm and inviting setting for holidays and special occasions. Relax in the spacious living room, unwind by the wood-burning fireplace in the cozy den, or enjoy movie nights and game days in the separate oversized family room. With five generously sized bedrooms, there’s plenty of space for family, guests, or a home office. Step outside and discover your own backyard oasis. Multiple decks extend the living space outdoors, creating the perfect setting for barbecues, celebrations, or quiet evenings under the stars. The inground freshwater pool invites you to enjoy summer days in style, while the lush gardens, colorful flowers, and mature plantings add beauty and tranquility year round. An amazing standout feature is the large 2 car barn in the backyard, ideal for hobbyists, gardeners, workshop space, extra storage, or parking additional vehicles. This incredible property offers the rare combination of indoor comfort, outdoor enjoyment, and versatile space, all in a setting that feels both welcoming and private. IGS, CAC, 150 Amps

28 Cygnet Drive, Smithtown
$1,890,000
4 Beds ⋅ 3 Baths ⋅ 1008414 MLS
Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a professional contractor as his personal home with attention to detail and premium materials throughout. Situated on a private 1-acre property, this exceptional 4-bedroom, 2 1/2 bath home welcomes you with a striking stone façade and dramatic arched entryway that sets the tone for the extraordinary craftsmanship found throughout. Features include oak hardwood floors, solid hardwood interior doors, custom millwork, marble and tile mosaics, a custom detached 2-car garage with handcrafted garage doors built by the homeowner and features its own electrical panel. The fully finished basement includes an outside entrance, laundry area and epoxy flooring. The large, open kitchen includes custom cabinetry, granite countertops, stainless steel appliances, and custom designed tile work. A breathtaking handcrafted marble fireplace with carved lion statuary serves as the centerpiece of the home and features a heat-circulating system with dedicated venting to the primary suite above. Built with 2x6 construction and blown-in insulation for exceptional energy efficiency, the home was also strategically positioned above grade to promote superior drainage. Smart home features include remote thermostat controls with separate zones in each bedroom and an automatic leak-detection water shutoff system. Extending the living space outdoors, a covered patio overlooks the private grounds and is already pre-wired for cable and has a water line in place, providing a seamless opportunity to create the outdoor kitchen and entertainment area of your dreams. From the handcrafted architectural details to the thoughtful engineering and modern conveniences, no expense was spared in creating this truly exceptional residence. A rare opportunity to own a luxury home unlike anything else on the market.

225 Old Willets Path, Smithtown
$1,699,000
4 Beds ⋅ 8 Baths ⋅ 1008427 MLS
Built in 2010 by Quality Features Inc. to a specification meaningfully above the base community standard, this is a 4,610-square-foot colonial on three above-grade levels with a full walk-out basement, three-car attached garage, and a build quality that is visible in every room: oak, marble, and porcelain floors throughout; custom millwork and moldings on every level; Wolf appliances and granite counters in the kitchen; three gas fireplaces, including one anchoring the Lynx outdoor kitchen on the rear terrace; a whole-house generator sized for a home this large; and a residential three-stop elevator serving all levels. The home is fully ADA-compliant and handicapped accessible, engineered into the original build from the foundation up, not retrofitted as an afterthought. The entry foyer establishes the scale immediately — two-story ceiling, custom staircase, hardwood flooring, millwork that carries through the entire main level. The kitchen is organized around Wolf cooking equipment, Sub-Zero-class refrigeration, granite counters, and custom cabinetry built to ceiling height. The rear of the house opens to the pond from the kitchen and main living areas — the sightline was designed deliberately, so the view is part of the daily experience of the home, not reserved for the terrace. Two gas fireplaces on the upper levels; the third anchors the outdoor Lynx kitchen, which turns the rear terrace into a four-season entertaining space with the pond as a backdrop. The lower level is a finished, walk-out floor in its own right. It houses an endless pool and resistance swim system, a dedicated spa room, and a full bathroom — with natural light, grade-level access to the rear yard, and direct sightlines to the pond. This is not a converted storage space. It is a fourth functional level with a specific purpose. Four bedrooms, seven full baths and one half bath. Every bedroom has a private bath. The primary suite is pond-facing on the upper floor. Ten total rooms. The three-stop elevator eliminates the vertical movement problem that makes most three-story homes harder to live in than they look on paper — groceries, luggage, laundry, and daily circulation across levels all become straightforward. The accessible design and flexible floor plan make this home genuinely adaptable across any configuration of use. Hamlet Estates is a gated community of approximately 85 homes with 24-hour guard-staffed entry, a 9,300-square-foot clubhouse, resort-style pool and spa, lighted tennis courts, full fitness center, basketball court, bocce, playground, lakeside putting green, and two community lakes with paddle boats. The pond this home sits on is one of them — a community amenity that 38 Hamlet Woods has exclusive proximity to. HOA common charges apply.

38 Hamlet Woods Drive, Saint James
$765,000
4 Beds ⋅ 2 Baths ⋅ 1010120 MLS
Welcome to 52 Brilner Drive in Smithtown, an Updated Expanded Cape, W/ 4 Bedrooms & 2 Full Bathrooms, located in the Highly Desirable Neighborhood Within the Smithtown School District. Ideally situated on a quiet dead-end street backing up to a Nature Preserve, this home offers exceptional privacy and tranquility. The Oversized Primary Bedroom on the First Floor features a spacious Primary Bathroom w/a Great STEAM SHOWER & His & Hers Closets, providing the convenience and comfort of main-level living. This home features a beautifully designed Front Porch w/ Blue Stone Flooring, perfect for a cozy sitting area, & a welcoming Entry Foyer w/ Vaulted Ceilings and a Skylight that fills the home with natural light. The spacious Living Room & Dining Room flow seamlessly into the Extended Eat-in Kitchen, featuring Stainless Steel Appliances, Corian Countertops, a Large Farm Sink, and ample cabinetry, w/ Andersen Sliding Glass Doors leading to a Large TimberTech Deck and a Fully Fenced Backyard. Additional highlights include: Brand New Driveway, New Boiler & Hot Water Heater ( Recently Converted from Oil to Gas), New Siding, Professionally Landscaped, In-ground sprinkler system, Newer Roof, 200 AMP Electric Service, Andersen Windows & Door, Oak Hardwood Floors Recently Refinished. The Second Floor offers two additional Bedrooms. The Full-Size Basement, Partially Finished W/ Outside Entrance. This is the one you’ve been waiting for: stylish, updated, and perfectly located! In a Prime Location Close to Great Shopping, Restaurants, Private Beaches, LIRR, Parks, Highways, Hospitals! A wonderful opportunity to own a beautiful home in desirable Smithtown!

52 Brilner Drive, Smithtown
$1,656,000
5 Beds ⋅ 3 Baths ⋅ 1010107 MLS
Nestled at the end of a private long drive shared with only 2 other homes and Not directly on Landing, this magnificent custom brick home offering Luxurious living space on a private 1.2 acre setting. features include a dramatic two-story grand entry foyer with two staircases, soaring vaulted ceilings, gourmet chef's kitchen with cherry cabinetry, granite countertops and Viking appliances, especially including Sub-Zero refrigerator, hardwood floors throughout entire house. Master suite with radiant heated floors, spa-inspired primary suite, and beautiful views of preserved land, Designed for elegant entertaining and comfortable living with vaulted veiling and extra-large windows. Three high ceiling attached car garage with potential for double car lift storage. The full basement features high ceilings and a separate outside entrance, offering excellent potential for recreation, home office, gym, workshop or future finished living space. This exceptional residence combines timeless architecture, privacy. quite and premium craftsmanship.

589 Landing Avenue, Smithtown
$789,000
4 Beds ⋅ 3 Baths ⋅ 1002364 MLS
Welcome to this beautifully expanded Colonial nestled in the highly sought after College Section of Smithtown. This spacious 4 bedroom, 2.5 bath home offers the perfect blend of classic charm and modern updates. Step inside to discover gleaming hardwood floors, generously sized living spaces, and updated bathrooms designed with todays buyer in mind. The 372 square foot primary suite addition provides a wonderful retreat offering additional space and comfort rarely found in homes of this style. The thoughtfully designed floor plan is ideal for both everyday living and entertaining. A brand new roof (2025) and a young gas burner (2018) are just some of the improvements that provide peace of mind. Situated on .24 acre, enjoy a private backyard setting perfect for relaxing, gardening or hosting outdoor gatherings. A one car-garage, a full unfinished basement and muture landscaping complete the package . Located in one of Smithtowns most desired neighborhoods , this home offers convenient access to parks, shopping, restaurants, transportation all in Smithtown School District. With its spacious layout, desirable updates, and exceptional location, this is an opportunity you won't want to miss.

61 Hofstra Drive, Smithtown
$699,999
4 Beds ⋅ 3 Baths ⋅ 1008019 MLS
This classic 4-bedroom, 2.5-bath Center Hall Colonial on a quiet Nesconset cul-de-sac in the desirable Smithtown School District offers the space, layout, and location today's buyers are looking for. With many of the home's major improvements already completed, you'll have the opportunity to personalize the interior and create a home that reflects your own style. The main level features a light-filled living room, formal dining room, eat-in kitchen, and a den with sliding glass doors leading to the deck. A convenient half bath completes the first floor. Upstairs, you'll find an oversized primary ensuite with generous closet space, three additional bedrooms, and a full bath. An attached one-car garage and spacious Belgian block-lined double driveway add everyday convenience and curb appeal. Set on a beautifully landscaped quarter-acre corner lot, the property is accented by mature specimen trees, custom brick walkways, and thoughtfully maintained outdoor spaces that enhance its curb appeal. The big-ticket improvements have already been taken care of, including a roof that's just 7 years young, a burner replaced approximately 2.5 years ago, a recently replaced above-ground oil tank, and a 6-zone sprinkler system that keeps the grounds looking their best. Conveniently located just minutes from parks, shopping, local restaurants, and the LIRR, this home offers the rare opportunity to enjoy one of Nesconset's most sought-after locations while adding your own personal touches. Don't miss your chance to make it yours. Schedule your private showing today. TAXES HAVE BEEN GRIEVED.

2 Barrett Court, Nesconset
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 1006718 MLS
Welcome to your private 1.09-acre retreat, offering the perfect blend of comfort, space, and outdoor living. This beautifully maintained home features wood flooring throughout the main living areas, with tile flooring in the foyer, bathrooms, and laundry room for added durability and convenience. The spacious primary suite is conveniently located on the first floor and includes a walk-in closet and a private en-suite bathroom that features radiant heated floors. An additional first-floor guest bathroom provides added convenience for family and visitors. The large den offers a warm and inviting atmosphere centered around a cozy fireplace, making it the perfect place to relax year-round. The expansive kitchen is designed for both everyday living and entertaining, featuring abundant cabinet storage and generous workspace. Adjacent to the kitchen, the dining room impresses with cathedral ceilings accented by stunning wood beams, creating a bright and elegant setting for gatherings. The laundry room comes complete with a washer and dryer and is neatly enclosed with bifold doors. This room also boasts a radiant heated floor. Upstairs, recent renovations have added modern functionality and charm, including custom built-in shelving in one room and a dedicated built-in TV entertainment area in another. The upstairs bathroom has been tastefully updated with subway tile and a sleek glass partition. Step outside to discover an entertainer's paradise. The backyard showcases a massive 40' x 21' composite deck, ideal for hosting large gatherings, barbecues, and outdoor dining. Beyond the deck, you'll find an expansive 42' x 49' pool area featuring a beautiful L-shaped pool, creating a resort-like setting right at home. The property also includes a large storage shed and is surrounded by a secluded, private yard that offers tranquility and plenty of room to enjoy the outdoors. Set on an impressive 1.09-acre lot, this exceptional property combines spacious indoor living with incredible outdoor amenities, making it the perfect place to call home.

30 Landing Meadow Road, Smithtown
$839,000
5 Beds ⋅ 3 Baths ⋅ 1007352 MLS
The picture-perfect home with the white picket fence. Extensively renovated in 2022, this beautifully updated 5-bedroom, 2.5-bath residence blends charm with modern finishes throughout. Situated on a rare and expansive .67-acre property in the heart of St. James, the home features an open and inviting floor plan designed for both everyday living and entertaining. The main level offers a formal living room with fireplace, a spacious den with cathedral ceilings, and an open-concept kitchen and dining area. The kitchen is appointed with quartz countertops & custom cabinetry. Two bedrooms (possible first floor primary), full bath and a powder room complete the first floor, while the second level features three additional bedrooms and a renovated full bath. Nearly every aspect of the home was updated in 2022 & 2026, including the kitchen, bathrooms, windows, doors, siding, roof, fencing, mechanical systems, fixtures, and oil tank. The grounds offer exceptional outdoor space with expansive, level lawns, mature landscaping, a new paver patio, in-ground sprinkler system, and plenty of room for entertaining, recreation, or future enhancements. A detached two-car garage provides additional storage and convenience. A turnkey home offering the perfect combination of classic character, modern updates, and generous indoor and outdoor living spaces in a convenient St. James location. Will not last!

238 Woodlawn Avenue, Saint James
$4,999,000
993093 MLS
8.42 Acres with LI Sound water frontage and beautiful views. Please reach out to agent for more information regarding building and possible subdivision. Land being sold as is. Updated Survey expected shortly.

Boney Lane, Nissequogue
$799,000
4 Beds ⋅ 3 Baths ⋅ 1002477 MLS
Welcome to your Splanch Style Colonial located in a beautiful sidewalk community within the Smithtown School District. This spacious home offers a fully fenced private yard, 2-car garage with workbench area, and an inviting layout perfect for everyday living and entertaining. Step into the large entry foyer flowing into the formal dining room and updated granite counter kitchen with updated cabinetry. Convenient laundry area with outside entrance and powder room. Relax in the cozy den featuring a wood-burning fireplace and sliders leading to your private patio and backyard oasis. The floating living room showcases vaulted ceilings, skylights, and an abundance of natural light. The primary bedroom features hardwood floors and a full private bathroom, along with 3 additional generously sized bedrooms and another full bathroom. Finished basement offers additional living and entertaining space. This home has room for everyone — don’t miss the opportunity to make it yours!

33 Roy Drive, Nesconset
$3,790,000
5 Beds ⋅ 8 Baths ⋅ 1000931 MLS
Have you ever dreamed of building your own CUSTOM HOME in a small village on Long Island? Look No Further! Set within one of Long Island’s most prestigious and private villages, this extraordinary custom-built estate offers over 7,000 square feet of refined living space with an Elevator to service all Floors, First Floor Primary Suite, radiant floors, 2 Saunas, 2 steam showers, full basement with full bathroom and outside entrance, outside back porch with fireplace and full bathroom from outside only. Private setting on a breathtaking 2.35-acre wooded property, complemented by an additional one-acre private driveway. A seamless blend of timeless architecture and modern luxury, this residence has been thoughtfully designed with superior craftsmanship and uncompromising quality throughout. Home is completed to a point where we can schedule tours. A sweeping asphalt and stone driveway with cobblestone edging welcomes you to this impressive two-story traditional home. Inside, an elevator to service all floors of the home, soaring ceilings create an unparalleled sense of space — including a dramatic 20'6" two-story foyer and family room, 10-foot ceilings on the main level, and a full 10-foot walk-out basement offering endless possibilities. Main Level Elegance. The heart of the home is a spectacular chef’s kitchen featuring: * Custom cabinetry * Granite or Quartz countertops * Expansive center island with prep sink * Radiant-heated porcelain flooring Entertain effortlessly in the formal dining room with built-in cabinetry, elegant millwork, and premium stone surfaces. The two-story family room showcases a modern linear gas fireplace beneath a coffered ceiling, creating a striking focal point. An en-suite bedroom provides flexibility for guests or extended family. Additional highlights include a radiant-heated powder room and a covered rear porch with gas fireplace — perfect for year-round outdoor living. Upper-Level Retreat: The second floor features **four en-suite bedrooms**, each with custom closet systems and wide White Oak flooring. The primary suite is a sanctuary, boasting a spa-inspired bath with a large steam shower, radiant heated floors, and deluxe Kohler fixtures. Exceptional Construction & Infrastructure: Built for longevity and performance, this estate includes: * Engineered wood web floor joists *Oversize 3 Car Attached Garage * 400-amp electric service * Natural gas service for heating, hot water, dryer, future generator & pool * Public water via Suffolk County Water Authority * Seven oversized drywells for optimal drainage Throughout the home, meticulous detailing includes wide White Oak hardwood flooring, heavy base moldings, chair rail and crown moldings, and an extra-wide custom staircase with open railings. In-ground Pool is an option and can be customized. 3D Reality Tours are samples of the builders work, not the exact same model we are building. A rare opportunity to own a masterfully constructed estate in one of Long Island’s most exclusive enclaves — where privacy, luxury, and timeless design converge.

550 Moriches Road, Head Of Harbor
$1,095,000
4 Beds ⋅ 3 Baths ⋅ 1001456 MLS
Set on .61 acres of flat, beautifully landscaped property in the Hamlet of St. James, this well maintained center-hall Colonial combines timeless charm with spacious living and thoughtful recent updates throughout. The formal living room, dining room, and oversized den are filled with warmth and character, featuring wide-plank pine flooring and generous entertaining space. The den is anchored by a charming wood-burning fireplace, creating the perfect setting for cozy evenings and gatherings. The sun-filled kitchen offers oak cabinetry and is centered around a large island, with a bright breakfast area and sliding doors that open to the backyard oasis. The spacious primary suite provides a peaceful retreat with a walk-in closet and a recently renovated spa-like bath featuring an oversized shower and double-sink vanity. Three additional bedrooms offer wall-to-wall carpeting over hardwood flooring and include custom closet systems. Additional highlights include a large unfinished basement ideal for storage or future finishing, recent updates to the roof, central air conditioning, and bathrooms, offering comfort and peace of mind for years to come. Step outside to your private fully fenced resort-style backyard, complete with an inground saltwater pool with new salt system and paver patio perfect for summer entertaining, relaxing weekends, and outdoor living at its finest. Nearby is local shopping, area beaches, fine dining, and Stony Brook University and Medical Center. Smithtown Schools.

41 Astor Avenue, Saint James
$669,999
4 Beds ⋅ 3 Baths ⋅ 1001234 MLS
Contract Vendee, As-Is, 4 bedroom, 2.5 bath colonial with full bsmt and 2 car garage on 1/2 acre in Smithtown East SD. First floor features, Living Rm, Dining Rm, EIK, 1/2 bath and Family Room. Property requires full renovation.

7 Michael Place, Nesconset
$775,000
5 Beds ⋅ 2 Baths ⋅ 992164 MLS
Stunning 5 possible 6-Bedroom High Ranch in Smithtown East Schools: Welcome Home To This Sprawling And Impeccably Maintained 5-Bedroom, 2-Bathroom High Ranch, Perfectly Situated On An Expansive, Oversized Property Including An Additional Lot. Boasting Incredible Curb Appeal And An Oversized Driveway. This Residence Offers The Rare Combination Of Spacious Interior Living And A Massive Outdoor Oasis. The Heart Of The Home Features A New Updated Gourmet Kitchen Equipped With Modern Finishes, including Soft-Close Cabinets, Stainless Steel Appliances, Center Island, And Quartz Counter Tops, Seamlessly Flowing Into Bright, Open Living Spaces. Both Full Bathrooms Have Been Recently Renovated With Stylish, Contemporary Fixtures. With Five Generous Bedrooms With Ample Closet Space, A Formal Living Room, Dining Room, And Family Room. There Is Ample Space For A Home Office, Guest Quarters, For A Growing Household. Step Outside To Your Private Retreat, Featuring A Sparkling Inground Swimming Pool Surrounded By Professional Landscaping And Vast Green Space, Plus A Screeded-In Patio Space Perfect For Entertaining Or Peaceful Relaxation. Located In The Highly Sought-After Smithtown School District, This Move-In-Ready Gem Offers The Perfect Blend Of Luxury Living, Comfort, And Prime Location. Don't Miss The Opportunity To Own This Unique, Oversized Property!

4 Florence Street, Nesconset
$6,800,000
5 Beds ⋅ 10 Baths ⋅ 000034 MLS
Waterfront – Set along 243’ of pristine Long Island Sound frontage, this extraordinary waterfront estate offers a truly rare combination of sweeping unobstructed water views, direct access to a sandy beach, and beautifully manicured level grounds with no high bluff — creating an unparalleled coastal setting rarely found on the North Shore. Privately nestled at the end of a private cul-de-sac on 2 lush acres, this over 7,000 square foot custom residence plus an unbelievable entertainment lower level is surrounded by magnificent specimen plantings, manicured gardens, and expansive Ipe Brazilian walnut decking designed to embrace the breathtaking waterfront backdrop from every angle. Nearly every room captures stunning water views, creating a seamless connection to the shoreline while filling the home with natural light and tranquility. Custom built with uncompromising quality and craftsmanship, the residence showcases high-end custom finishes, exquisite detailed moldings, elegant designer touches, and only the finest materials and systems throughout. Sophisticated yet inviting, the home offers an exceptional blend of refined luxury and relaxed coastal living. Every detail has been thoughtfully curated with no expense spared. Designed for both grand-scale entertaining and intimate everyday living, the property offers exceptional indoor and outdoor gathering spaces where unforgettable memories are waiting to be made. Enjoy breathtaking sunsets over the Long Island Sound with unobstructed views stretching to Connecticut, all from the privacy of your own extraordinary waterfront retreat. Ideally located approximately 60 miles from Manhattan and moments from fine dining, shopping, marinas, Stony Brook University, and Stony Brook University Hospital, the property offers a rare blend of private coastal living and everyday convenience A true private oasis, this remarkable estate offers the feeling of being worlds away while enjoying the beauty, serenity, and prestige of luxury waterfront living at its absolute finest.

6 Pheasant Run, Nissequogue
$2,650,000
6 Beds ⋅ 6 Baths ⋅ 999556 MLS
SELLER MOTIVATED! Welcome to this exceptional new construction estate nestled on 2 private acres in the heart of Nissequogue, one of Long Island’s most prestigious Gold Coast communities. This stunning residence offers exclusive beach access and is conveniently located just 3 miles from the Saint James and Smithtown LIRR stations, providing easy access to New York City. Designed with timeless elegance and modern sophistication, this custom-built home features a sun-drenched open floor plan with soaring ceilings, oversized windows, wide-plank white oak flooring, graceful arched doorways, and two gas fireplaces adorned with custom stonework. The gourmet chef’s kitchen is the centerpiece of the home, showcasing custom cabinetry, premium Thermador appliances, an oversized center island, a butler’s pantry, and a formal dining room complete with dual wine refrigerators perfect for entertaining on any scale. Offering 6 bedrooms and 5.5 bathrooms, including luxurious primary suites on both the main and upper levels, every detail has been thoughtfully curated with elevated designer finishes. Each bathroom offers its own distinctive character, featuring custom vanities, exquisite tile selections, elegant stonework, and beautifully designed walk-in showers that create a spa-like experience. Designer lighting and crystal-inspired hardware add warmth, sophistication, and refined detail throughout. The grand upstairs primary suite boasts vaulted ceilings, dual walk-in closets, and a spa-inspired bath featuring a soaking tub and oversized glass-enclosed shower. Additional amenities include a full basement, 2.5-car garage, and a private tree-lined setting surrounded by protected nature preserves. A rare opportunity to own a remarkable luxury residence that seamlessly blends modern design, superior craftsmanship, and the tranquility of North Shore living.

9 Wilderness Road, Nissequogue
$749,000
5 Beds ⋅ 2 Baths ⋅ 956909 MLS
Great Hi Ranch with 2 Sep Living Areas plus Garage, Fenced Yard, Oversize Driveway, Smithtown Schools, Central Air

106 Summit Drive, Smithtown
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 996959 MLS
Experience a true vacation-at-home lifestyle in the heart of the Village of Nissequogue, where every day begins with breathtaking southern water views and ends with spectacular western sunsets from a private beach just moments from your doorstep. Nestled within an exclusive beach community with private beach access (dues required), this exceptional coastal retreat seamlessly blends timeless architecture, sophisticated design, and effortless indoor-outdoor living. Beautifully crafted with a classic cedar shingle exterior, this one-of-a-kind residence showcases panoramic water views from multiple balconies and exceptional attention to detail throughout. Sun-drenched living spaces feature soaring vaulted ceilings, white oak flooring, and expansive windows that capture the beauty and serenity of the surrounding landscape. A wood-burning fireplace creates a warm and inviting focal point, while motorized shades in the living room, kitchen, and dinette area provide everyday comfort and convenience. The chef's kitchen is designed for both everyday living and elegant entertaining, featuring custom cabinetry, a Cooper farmhouse sink, induction cooktop, and premium designer finishes that elevate the space. Step outside to your private outdoor oasis, complete with a spacious deck, retractable awning, outdoor shower, beautifully landscaped grounds, and an in-ground sprinkler system. Whether hosting summer gatherings, enjoying sunset cocktails, or returning from a day at the beach, these thoughtfully designed outdoor spaces are ideal for relaxing, entertaining, and unwinding. The third-floor primary suite is a true seaside sanctuary, offering a private balcony with sweeping water views, a luxurious en suite bath, and custom maple-finished closets with built-in maple drawers. Imagine beginning each morning with coffee overlooking the bay and ending every evening with unforgettable sunsets. Exceptional amenities include radiant heated tile flooring throughout the first floor, heat pump systems servicing the main and third floors, smart thermostats, a Ring doorbell system, Kohler generator, recessed hinges, European magnetic door strikes, and sprinkler protection for third-floor exit access. Additional highlights include a two-car garage, U-shaped driveway, and an unbeatable North Shore location. Enjoy close proximity to Long Beach Town Park, just 0.6 miles from Smithtown Bay Yacht Club and approximately 6 miles from the St. James Long Island Rail Road station. This rare offering captures the essence of refined coastal living in one of Long Island's most sought-after waterfront communities. More than a home, this is a year-round retreat where luxury, tranquility, and breathtaking surroundings create an unparalleled lifestyle.

14 Beach Plum Lane, Nissequogue
$10,800,000
5 Beds ⋅ 8 Baths ⋅ 996747 MLS
The great statesman, Daniel Webster, (January 18, 1782-October 24 1852) famously remarked, “Long Island Sound is our American Mediterranean.” Indeed, it is. Summerwind. This waterfront enclave, nestled along a uniquely picturesque stretch of Long Island Sound, boasts epic sunrise and sunset views. With architecture and design by world-renowned CetraRuddy Architects, the carefully curated plan demonstrates timeless elegance and understated luxury. The exterior, clad in white stucco and trimmed in fossilized Atlantic shell stone, is complemented by a striking clay tile roof; a design painstakingly supervised by Ludowici’s renowned Master color specialists. Double 11-foot-tall iron entry doors open into the 50-foot-long entrance hall; its intricately carved, painted wood ceilings, soaring to a height of 24-feet, make an indelible first impression. The antique black and white marble and European smoked oak herringbone floors throughout exude Old World charm, and the hand-forged iron balusters and intricately hand-carved rails of the staircase add a touch of whimsy. Entertaining is a delight in the banquet-sized dining room, where a 17th-century Louis XIII limestone mantel takes center stage, complemented by a wet bar, wine refrigeration, and seating for up to 24 guests. The kitchen is the heart of the home and a chef's dream, featuring a raised fireplace hearth finished with 300-year-old French clay tiles, ideal for wood-fired cooking. The expansive custom cabinetry with brass Waterworks hardware provides abundant storage, with a suite of top-of-the-line Wolf and Sub-Zero appliances. The library boasts a dazzling 1920s Baccarat chandelier and a wood-burning fireplace framed by a meticulously carved stone mantel from Orvieto, Italy, circa 1710. The sunken music room, framed by an entire wall of windows, overlooks Long Island Sound, offering the best interior perch for the most epic golden sunsets. The south-facing Moroccan-themed conservatory is bathed in sunlight from the early morning until mid-afternoon, making for very satisfied plants overwintering in this warm, happy space. By evening, the soft glow of a Murano fixture circa 1940 transforms the room into a moody gathering place. Each of five bedrooms offers en suite baths and outdoor space overlooking the breathtaking Long Island Sound. (Two of the five bedrooms have wood-burning fireplaces). An extraordinarily appointed lounge, inspired by Ralph Lauren’s legendary Polo Bar, defines the lower level of the home. Additional amenities here include a soundproof screening room, full wet bar, a professionally audio-tuned listening lounge for vinyl buffs, fitness room with traditional and infrared sauna, expansive laundry room, 3-car garage, and another en suite bedroom, ensuring every need is met in this exceptional home. The grounds of this very private property include a treillaged rose garden, a stone fire pit, Italian wrought iron day beds, a full outdoor kitchen by Hestan, and a private beach with retractable access stairs. Situated equidistant between Long Beach and Short Beach on Long Island's tony North Shore, any and all aquatic activities are readily available, including nearby docking and mooring rights. Other featured local attractions include the beloved Saint James General Store (a fixture on the National Register of Historic Places), Harmony Vineyards, Avalon Nature Preserve, canoeing and kayaking on the Nissequogue River, equestrian facilities, a private golf club, and boating on Long Island Sound. Broker/Owner.

Nissequogue
$1,199,999
993325 MLS
BUILD YOUR DREAM HOME!!!!!! A rare find....flat piece of land in the Incorporated village of Head of The Harbor. This property is surrounded by 4000-7000 sq foot homes. There is electric, water and gas at the property. Ideal location close to Stony Brook Hospital, and major roads.

Timothy Road, Head Of Harbor
$1,999,999
5 Beds ⋅ 5 Baths ⋅ 992489 MLS
Welcome to this spacious 5-bedroom, 5-bath Colonial set on 1.70 acres in the desirable Head of the Harbor section of Saint James. This 4,788 sq ft home features a functional layout with a first-floor bedroom and full bath, formal dining room, living room, and an open kitchen with granite countertops, center island, and eat-in area leading to a large family room with fireplace. The second level includes a primary suite with walk-in closets and a private bath, along with additional generously sized bedrooms. Additional highlights include hardwood flooring, crown molding, high ceilings, central air, and natural gas heating. The full finished basement offers additional living space with a lavatory. Exterior features include a 3-car garage, private driveway, and an in-ground pool. Conveniently located near major roadways, shopping, and Smithtown schools.

2 Deepwells Lane, Saint James

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